A Very Hands-On Situation
by I'mtheAlphahearmeRoar
Summary: Stiles gets a dildo stuck up his ass. Derek to the rescue!


Being an Alpha isn't an easy job, it takes leadership and a lot of responsibility. You need to know how to communicate with your pack, not just to communicate with the Betas as a whole—a group—but also to communicate with them individually. Alphas aren't just there to order around their Betas, they're there to be their friend as well. An Alpha holds a certain amount of trust, someone who the Betas can entrust their life with if a situation takes a deadly turn of events. For that—for a Beta to trust their Alpha—the Alpha needs to get to know each one of their Betas personally. Connect with them. Only then, can a strong bond be formed. If that bond between Beta and Alpha is strong it then travels throughout the pack and begins strengthening the other Betas as well. It changes the whole meaning of Pack. Not just a pack anymore, but a family.

As an Alpha, one of Derek's highest priorities is to have the pack—his family—feel safe and comfortable around him. He wants them to feel like they can tell him everything and anything, whether it being about a new person in town that they think could turn out to be an eventual threat to Beacon Hills, or just trivial problems where they need relationship advice or require help with homework. Derek there's for moral support. He's there to be a mature adult figure that they can rely on whenever they need him. Not just for the werewolves in his pack, but also for the humans as well.

_Stiles_.

Stiles is one of four humans in his pack. Lydia, Danny and Allison are too. But Stiles, Stiles is the only human in his pack that seemed to take Derek's 'Alpha priorities' seriously. Maybe a little _too _seriously.

He could never forget the time Stiles had texted him for help. It was literally branded in his mind, a corner of his brain so deep that no amount of trying to forget would erase it… Not that he'd ever _want _to erase it, though.

Derek had been lounging on the couch of his loft with the lamp's soft light filling the room, reading a book when his phone had vibrated in his pocket. With a sigh he thumbed the page's edge for a keep safe bookmark, slipping the book shut and placing it on the coffee table spine up. He slid his phone out of his back pocket, opening the text.

**_sourwolf need ur help – S_**

Stiles needed his help. Shit. What could the kid have done this time?

_Stiles? What is it? What's wrong? – D_

**_i'm stuck and i mean like seriously stuck so i need u 2 come help me – S_**

"He's _stuck_," Derek snorted, shaking his head.

_Stuck? Stiles, stuck how? Where are you? – D_

**_doesn't matter and i'm at home now please hurry dude – S_**

Okay, that had got his attention. Stiles' texts were rushed and also, he never said _please _unless it was absolutely necessary. So whatever this was, it was important.

Derek didn't think, didn't care that it was well past nine o'clock at night, just drove over to the Stilinski residence in a hurry, speeding at least half of the way. He ended up parking a street down, sprinting up to the premises and vaulting the side of the house. When he got to the ledge of Stiles' window he found that the window was closed and locked.

"Stiles!"

He banged his fist on the window and then waited for something. Anything. A sign that Stiles was in there, that Stiles could hear him.

No answer.

He tried again.

"STILES!"

Still no answer.

Derek growled, feeling the wolf in him coursing through his veins. His wolf was a rumbling force in his chest, a magnetic pull in his mind, and a tugging sensation in his stomach. It was panicking. _He _was panicking. One of his pack was in trouble and he couldn't even get _in_ to help them.

Derek didn't have the time to wait any longer. Stiles could seriously be hurt. He'd said that he was stuck but that could also mean something else, something bad. Stiles was one of the most cryptic people he knew. So with one foot he kicked the window open, boot smashing completely through the glass. He wasted no time in climbing inside, too riled up in his worry that Stiles could be hurt to care about the pain when a glass shard slashed into his arm. It would heal in seconds anyway.

The room was dark and empty, Stiles' bed unmade with the covers halfway shucked over the sides. Stiles' laptop was also on, dimmed glare of the Captain America desktop screen the only light in the room. Derek noticed the bedroom door was closed, and when he tried to open it he found that it was locked.

"Dammit," Derek muttered, rattling the doorknob, and when that didn't work twisting and pulling at the doorknob with both hands. "Stiles!"

"…over here."

Derek's hand clenched around the doorknob, wolf rumbling in his chest when he heard the soft voice coming from somewhere behind him. It was at that moment he realized that he hadn't once tried to scent the room when he'd arrived. He closed his eyes, inhaling through his nose. Immediately he caught the scent of Stiles that had eluded him moments before. It was stronger than usual, musky and traced with a hint of sweat.

He turned around, hand loosening and falling away from the doorknob. He took a glance around the room, letting his irises bleed red. The darkness that swept over the room was no match for his heightened eyesight and everything around him soon became visible, illuminated like he was looking through red tinted camera lens. It was only when he trained his eyes to the farthest corner of the room did he find Stiles huddled up against the wall with a pillow over his… crotch.

"Stiles." The boy looked up, eyes wide and lips parted. Derek saw—even with his red highlighted vision—that Stiles had a blush flushing over his cheeks. "Stiles, what's going on?" he asked, cautious edge to his voice. When Stiles didn't reply, just stared at him bug-eyed, Derek slowly took a step forward. "Stiles, I can't help you if you don't tell me what's going on. You said you were-"

"Stuck." Stiles' voice wavered when he spoke. "Yeah, I'm— I am."

Derek sighed, not sure what to think. Stuck could mean many things, though not many fitted in the category of 'sitting on the floor of your bedroom, in the dark, with a pillow over your crotch.' Unless...

_Oh._

The smell of musk and sweat Derek had smelt earlier which, when he checked, was still permeating the air, was probably the first thing that should have clued him in to what he was dealing with. What Stiles' _stuck _situation was.

"Please. Tell me you _didn't_." Stiles bit his lip, worrying it between his teeth as his eyes flickered down to the ground in embarrassment, his fingers that were clutching the pillow curling around the edges of the material. "Stiles..."

"I was just trying it out! It was fine until—" He lifted the pillow hesitantly, closing his eyes and turning his head away. "Until it got stuck…"

Derek could only stare, feeling strong sympathy for the kid as his mouth turned dry.

Of course Stiles would get a dildo stuck in his ass.

"How long—" He stopped himself before his voice could crack, clearing his throat quietly as he knelt down beside Stiles. "How long has it—?"

"Nearly two hours," Stiles sighed, wincing when he shifted his knees. "I tried to, y'know, take it out. But, uh— I kinda just ended up pushing it further in…"

"And you want me to—" Derek coughed. "Help?"

Stiles' nose scrunched up like what he was about to say physically pained him. Well, unless it was the dildo stuck in his ass. Probably was. "Trust me dude, if I could get _anyone_ else to help me, I would. But, um, if you haven't realized." He waved his hand in the general area of his crotch. "Dildo. In the ass. Don't think anyone would want to get up close and personal to _that_."

"So you thought you'd just text me, get me to come over, and have me help you take it out," Derek deadpanned.

"Uh, _ha_, well when you put it like _that_." Derek arched an eyebrow and Stiles sighed, shoulders slumping. "Yes. Yes I did." When Derek just huffed, he frowned. "Hey! Don't think that this isn't as awkward for me as it is for you. Because it is! You have _no_. _Idea_."

"Believe me, I have a pretty good idea," he groaned. Stiles' made a surprised noise in the back of his throat, lips quirking up in a small smirk.

"Did you—"

"Shut up," Derek growled. "I'm not here to talk about me. I'm here to… help you." He tilted his head to the side, looking down at Stiles' ass at a different angle. "I still have no idea how you got that stuck up there, it's pretty big."

Stiles snapped his mouth shut to hold back his undignified squawk. "Hey! But yeah, I guess it is." The flush on his cheeks grew more red than pink. "Um, I've found that small ones don't really… do the trick."

"Okay." Derek nodded. He understood. When he was younger, he found out the same thing. He hadn't got the thing stuck up his ass though… Well, not for _this _long. "Have you tried bearing down?"

"What? Like a _pregnant _woman?" At Derek's scowl, he sighed. "Yes. Yes I tried. It didn't work."

"Jumping up and down?"

"_Seriously?_"

"Yes."

"Uh… No?"

"Try it."

Stiles blanched. "No way, dude. I am _not _doing that."

Derek shrugged. "Fine, if you want it stuck up there forever…"

Stiles' blanch turned more into a look of pure horror, blush sinking away as his face paled. "I don't want this stuck up here forever. Oh my god."

"Then try jumping up and down. If it comes out, I won't have to stick my hand up your ass."

That time Stiles _did_ squawk. "Y-You what?"

Derek huffed. "Just try it, Stiles."

"Okay, alright. I'll jump up and down like a fuckin' rabbit in_ heat_ if it helps this thing come out." He got himself up, hissing and hiding a small wince—not that Derek didn't see it—as he steadied his shaky hands on the closet behind him as he stood up straight.

Derek watched Stiles with a blank face even though truthfully, all he really wanted to do was help the kid out and save him the pain by just removing it for him.

"Okay, I'm _not _jumping up and down with you staring at me." Stiles looked down at Derek sitting on the floor in front of him, expression emotionless and staring back up at him. The guy's face was in eye level of his genitals and Derek could really just sneak a close up peek at them very _easily _if he decided to drift his eyes downwards a little bit further. Yep, he did. Fuck everything. "Or, well, staring at my dick. Anyway! Get out." Stiles pointed to the door.

Derek remained sitting, not moving. "Stiles, you're being ridiculous."

"I'm being ridic— _No_. No I'm not. Seriously dude, this is a _no go_. Me not jumping if you not leaving." Stiles glared at Derek even despite the childish attitude that he was showing, hoping the guy would just take a freakin' hint and leave already so he could get this show on the road. The sooner this thing was out of his ass, the sooner he could crawl under his bedcovers and hide away from the world in embarrassment for the rest of his life.

"I'm not leaving. If that thing doesn't come out, I'm going to have to go in. Also, watching you jumping up and down wouldn't be as humiliating as what I've seen of you already," Derek stated flatly.

It took a few seconds but eventually Stiles deflated, the riled-up look in his eyes slowly growing weaker and weaker until it was nothing but a sad look of defeat.

"You're right. Fuck. You're _totally _right," Stiles groaned. He looked down at the ground, seeing the pillow and bending down to pick it up, placing it over his crotch. "I'm still using this. I'm _not _letting you see my bouncin' balls."

Derek snorted. "It wouldn't be the scariest thing I've seen." Before Stiles could squeak a response he held his hand up. "Just go. Jump."

"But you—you just said…"

"_Jump_."

"Okay, okay. _Yeesh_." Stiles secured the pillow over his crotch, holding it there tightly, before taking a deep breath and jumping up, then down again, up then down again, up then— "Ow, ow, _ow_. Okay, I can't—I can't do this," he yelped.

Derek clenched his jaw, holding himself back from wrestling the kid down onto the bed and driving his hand in there and taking it out. "What is it?"

"It _hurts _is what is it," Stiles whined. "I can't Derek, okay? Whenever I jump it feels like someone is literally _kicking me_ _up the ass_."

Derek actually winced. He knew the feeling. "Alright, I didn't want to do this," he oh so totally _did,_ "but I'm going to have to take it out. Lay down on the bed."

Stiles made an absolutely pitiful noise in the back of his throat. _Not as pitiful as the sounds he's going to be making when I've got my hand shoved up his ass_, Derek thought as Stiles waved his arms about like he was having a mini freak-out attack episode.

"Lay down on the— Oh no. _No_. No I am _not _letting you put _that_," he pointed at Derek's large hand, "up my butt. Nope, nu-uh. Not happening, buddy.

Sometimes Derek wished that Stiles was like any other _normal_ human being, but no. He had to overreact with everything.

"Stiles, this is the final option. It's either I take it out, or it stays in there." He left a pause for dramatic effect. "Forever." Another pause, plus a small smirk that he can't keep buried down anymore. "You know, I've heard that forever is a long time. And Stiles, I don't really think you'd be able to put up with that thing nestled in there fore—"

"_Ugh_, just shut up! Shut _up_!" Stiles put both hands over his ears, mouth screwed up in a horrible grimace. "Oh my god. I hate you, Derek. I. HATE. YOU."

"Oh, so you hate me. Okay. Well, I guess that means you don't really want me to help you then, huh?" Stiles unblocked his ears and his mouth fell open in an O that was a mix between shock and stupor. Derek chuckled. "Don't worry, I understand. It's perfectly fine," he shrugged, flashing a wicked grin. "Have a nice night, Stiles." He stood up and started walking towards the window, was just about to put his foot over the wrecked glass and step one foot onto the roof when Stiles cried out a "_Wait_! Derek, wait! Please don't go!"

Derek turned around, observing Stiles' face that was now flushed pink like earlier. "Yes, Stiles? Anything I can do for you?" He smiled nicely—maybe a little bit too nicely—and crossed his arms over his chest, waiting for a reply.

Stiles muttered a curse. "Just do it."

Derek could hear the kid's heart beating a mile a minute.

"Just do _what_, Stiles?" he teased. He couldn't help but play with the kid a bit. It was always priceless.

Derek didn't think Stiles would actually say it, and not _like that_, but nevertheless he did manage to, even if it _was _said with the trace of a shy quiver in his voice.

"Please, take the dildo out of my ass," Stiles muttered, pink flush not pink anymore but scarlet.

Derek caught the choking cough in his throat before it managed to leap out of him. He nodded once, slowly, walking over to sit on the bed and patting the spot in front of him. "Lay down," he said, watched Stiles hesitantly walk over, pillow still held over his genitals as he lay down where Derek had indicated, crossing his legs underneath him.

"No. Don't do that." Derek pointed to Stiles' legs. "Spread them out."

"Why?" Stiles asked shakily, shy with embarrassment.

Derek sighed. "Because I can't get to it with you lying like that. Now spread them. And take that damn pillow away."

Stiles groaned, spread his legs out and took the pillow away slowly, hesitantly. When it was gone he closed his eyes, turning his head away and burying it into the mattress shamefully. "There. No pillow. Legs spread," he said, voice muffled by the mattress. "Now hurry up and take it out before I die of humiliation."

Derek resisted the urge to run his hand through Stiles' hair soothingly, to pet the shame right out of him, instead taking a look down at what he needed to deal with. Stiles' hole was stretched, stretched wide enough that Derek could see right up the kid's ass like a tunnel. The dildo was wedged up deep and Derek would just make out the end of it. It was red.

"Red for Little Red. Should have guessed," he mused, chuckling when Stiles buried his head further into the mattress and whined. "Alright. Stiles, I'm going to try and take it out now. Is that okay?" he asked. Stiles just nodded and he took that as a good enough answer as any.

Derek very slowly put in his index finger, and Stiles whimpered when it entered him straight away. Derek almost let out a small whimper himself when he added the second finger, finding out that just like the first, it slipped in without any need of necessary pressing or pushing. Stiles' ass was stretched out wide enough and slicked with enough lube that his fingers slid inside easily. By the time he was up to his fourth finger Stiles' ass was clenching around all four, muscles fluttering and pulsing around the girth of them. Derek just couldn't resist, pulling them all out before pushing them back in, in one slick slide. Stiles' small and quiet moan was muffled by the mattress, but Derek could still hear his heavy shaken breathing as he did it again and again, wet sound of his fingers entering and existing Stiles' hole driving him and his wolf crazy. What drove him even more crazy was when he saw a white glob of pre-come spurt out of the slit of Stiles' cock, and he inhaled sharply, heady smell of salt and filling his nostrils.

"God, _fuck_ Stiles. You're so stretched. So open for me." He groaned before he could stop himself, pushed and pressed his fingers in deeper, sliding them in and out in fast non-rhythmic movements. Stiles started moaning unabashedly now, not caring to be quiet, and his face wasn't smothered in the mattress anymore so the noises of pleasure were loud and clear, not muffled and incoherent. Derek could feel his own dick hardening in his jeans, could feel the blood boiling underneath his skin as his wolf rumbled deeply in his chest.

Derek was so entranced, indulging in the silky wet heat of Stiles' ass and the constant little drawn out _ah's _and _oh's _leaving the kid's mouth that the motive of why he was doing this completely eluded him. It was only when the tips of his fingers made contact with something hard and plastic did Stiles make a high-sounding keen and Derek remembered what he was meant to be doing in the first place.

"Shit," he muttered, feeling like a complete idiot. He pressed his fingers in further, further enough so he could feel how the dildo lengthened out into a thick base. He wouldn't be able to grab it like this, though. He had to go deeper. "Stiles, I need to get deeper so I can get this out. Okay?"

Stiles groaned, a low-pitched noise that sounded almost wrecked. "Fuck. O-Okay. Dig deeper, sure."

Derek withheld a snort, instead pushing his fingers in deeper, fanning them out into a high-four, his thumb that was pressed against Stiles' rim the only finger missing from it being a high-five. He'd need to have his whole _hand _in Stiles to do that, and he doesn't think Stiles, let alone _him _would be able to deal with fisting right now. Especially _him_. He'd definitely lose control of the wolf if he saw Stiles' hole taking his entire hand, rim stretched to the extreme to accommodate his large fist, muscles gripping tight and sucking it whole into that moist cavern of slick-wet heat and— and he has to stop thinking about fisting Stiles and get on with what he's meant to be doing.

"I can feel the base. I'm going to wrap my fingers around it and take it out now, okay?" he said. Stiles made a small, choked noise in the back of his throat, but Derek still managed to catch the nod the kid sent his way. With Stiles' affirmation of further actions, he carefully curled his fingers around the base of the dildo before very slowly drawing it out an inch, then stopping to look up at Stiles' face to make sure what he was doing wasn't hurting him.

Oh, it most certainly did _not _look like it was hurting him. Not one bit.

Stiles' eyes were closed, his lips parted on a silent gasp. The moon outside was now positioned so that the moonlight was shining directly through the open window, casting its illuminate glow over the bed. It was because of this that Derek could see the flush on Stiles' cheeks without the darkness of the room hiding it. Derek could now actually trace the scarlet pattern that dotted his skin, streaking over his pale cheeks like red velvet. It was a beautiful sight, captivating, and when he drew the dildo out another two inches Stiles' eyes snapped open on a sharp hitch of a cry. Instantly Derek was met with two whiskey coloured eyes, the light of moon shading the orbs into a shimmering golden hue of amber, and he felt the wolf inside of him stirring and becoming restless.

"Oh my god, _Derek_," Stiles whined, his chest a rise and fall that matched his heavy breathing. "D-Don't take it out. _Fuck_. Please don't take it out."

Derek raised an eyebrow. "I thought that was the point," he said, drawing it out another inch, but automatically stopped when Stiles' breath hitched on a bitten out gasp that sounded almost like a mewl. "Wasn't it?"

"Y-Y-Yes, but change of plans," he groaned, rolling his hips in a small forward-grind. "I want—I want you to fuck me with it."

Yep, Derek's wolf wasn't going to be contained for much longer.

"You—you want me to…" Derek's words trailed off before they even finished and he was pushing the dildo back in, deeper than it had been before he'd gotten his fingers around it. All of Stiles' breath rushed out of him in a loud shout, back arching up and hips bucking, three dollops of pre-come leaking from the slit of his cock and spilling down the shaft. Derek caught a whiff of his scent with a sharp inhale, closing his eyes as the scent of sweet arousal and bitter salty pre-come overpowered and soaked into his senses.

"Fuck, _yes_, keep going," he moaned, and how could Derek say no to that? He pulled the dildo back, thrusting it forward again before setting a hard and fast in-out rhythm, watching the way Stiles' hands gripped the bed sheet in clenched fists, head thrown back and breathing out in little whimpered huffs.

"You like that?" Derek growled huskily, twisting the dildo on an inwards thrust, pulling it out all the way until only the tip remained in Stiles' hole and doing it again. Stiles nodded jerkily, panting heavily. "What does it feel like, Stiles? Tell me."

"B-Big, so big," he gasped, high choked grunt punched out of him when Derek pressed the head of the dildo against his prostate on a thrust. "_Ah_, o-oh my god. There, there, there. Right there, _fuck_."

Derek started to rub the head of the dildo against Stiles' prostate, pressing into it firmly and massaging the small gland, cursing softly and trying not to lose his self-control as Stiles' hole clenched to the stimulation. Stiles' body suddenly turned all akimbo, legs twisting in the sheets and spine arching, head rolling back and forth against the mattress as his hips bucked forward. Derek wondered if he could take more, couldn't help but wriggle his index finger in alongside the dildo, thrusting it in and out in time with each press of the dildo on Stiles' prostate.

The reaction was instant.

"Derek, _oh_, oh my god don't stop. Close, close, close. So close," he whined, breaths hitching out in sharp bursts.

"Mmhmm. You going to come for me, Stiles?" Derek fitted a second finger, pumping both in and out, watching Stiles' face go from slack pleasure to extreme bliss, mouth parted into an O. His eyes caught sight of Stiles' dick, the length of it pulsing, leaking a generous amount of pre-come that was pooling on his stomach. Derek smirked as he suddenly had an idea. He leant forward until his head was positioned right over Stiles' dick, the pre-come smeared head in close range of his mouth. "I know that before you said you didn't want me to look at your dick," he mused, glancing up to see Stiles' bewildered owlish eyes staring back, "but I'm going to do something even better." With that he bent his head, taking Stiles' entire cock into his mouth and sucking it down to the back of his throat.

"Oh my g— _oh my_—" Derek heard Stiles' words shatter themselves into garbled moans as he started to swallow around the boy's cock, moans soon dissipating into shrill whines, tempo of his _ah's _and _oh's_ rising. Derek knew it would all be over soon. He swallowed one more time, pressing the dildo in right up against Stiles' prostate. Just like that, Stiles was done. When it happened, it took all of Derek's willpower not to let the wolf off the leash, to allow it to howl in triumph that they'd _done this_. Stiles' whole body froze stiff for a a split second, then he started quivering, his whines coming out faster and faster until he surrendered to a loud, high-pitched keen. Derek felt the pulse of Stiles' cock all the way at the back of his throat, and he swallowed eagerly when hot spurts of come flooded his mouth. He kept swallowing, sucking on Stiles' cock until the last feeble drop was milked out, Stiles' choked sob a sign that he was too sensitive.

Derek backed off Stiles' cock, giving it one last lick as he removed his fingers from Stiles' ass along with the dildo, the boy's hole fluttering at the sensation. He placed the dildo on the bed beside him, before looking up at Stiles' face. That was when he lost it. Stiles' face was so open and unguarded, full plump lips red from being bitten and cheeks flushed, layered with a light sheen of sweat, and it had Derek's dick throbbing painfully hard in his boxer briefs, balls tingling. He shifted on the bed and winced, closing his eyes and breathing through his nose slowly. No. No he was _not _going to come in his pants like a teenager just because he'd got to make Stiles come, got to see what he looked like when he lost it and how his body trembled in orgasm and—

"D-Derek, are—are you okay?" Stiles asked, his voice hoarse and throaty. Derek opened his eyes and spared another glance up at him. And yeah, that was what did it. He grunted, gritting his teeth together to block the sound he knew he'd make, yet it came out anyway, as a small shaky whimper that he wished he could take back. But it was too late.

"Oh. My. God." Derek squirmed at the uncomfortable wetness in his jeans and braced himself for the oncoming shame, looking up to see Stiles staring at him, eyes wide like he couldn't believe what he'd just witnessed. "Did do you just—?"

"Yeah," he sighed. There was no point in lying. Lying was childish.

"Wow. Ha-ha, _okay _then." Stiles chuckled giddily before letting out a short laugh. "So like, that was your orgasm noise?"

Derek glared. "No."

"Oh, what, so that little whimper _wasn't _a 'oh my god I'm coming' sound?"

"_No_."

Stiles smirked, sitting up slowly so he could place a hand on the werewolf's shoulder. "Don't worry about it, buddy. I wasn't so crash-hot with mine either."

Derek clenched his jaw, keeping his own opinions to himself. The kid didn't need any more self-confidence or else he'd be bloody _radiating_ it. So instead, he rolled his eyes and told the kid to shut up. Because no, being immature wasn't childish at all.


End file.
